4-Methylphenyl isocyanate → HCID 9858766, compound

HRID 1698920Notes

Reaction equation

HRID 1698920 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[C:7]([C:6]1[CH:5]=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[S:3][C:2]=1[NH:1][C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([CH3:23])=[CH:15][CH:16]=1)=[O:22])(=[O:8])[NH2:9]

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 18322381HCID 18322381, compound

Product 1

HCID 9858766HCID 9858766, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-amino-5-tert-butylthiophene-3-carboxamide (0.14 g, 0.7 mmol) and p-tolyl isocyanate (0.093 g, 0.7 mmol) in toluene (5 mL) was stirred at 60° C. overnight. The reaction mixture was separated between with water (10 mL) and EtOAc (10 mL). The aqueous phase was back-extracted with EtOAc (3×10 mL), and the combined organic phases were washed with a saturated NaCl solution (25 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by chromatography (SiO2; gradient from 20% EtOAc/80% pet. ether to 30% EtOAc/70% pet ether) to give N-(3-carbamoyl-5-tert-butyl-2-thienyl)-N′-(4-methylphenyl)urea (0.092 g, 40%): 1H-NMR (CDCl3) δ1.38 (s, 9H), 2.32 (s, 3H), 5.58 (br s, 2H), 6.53 (s, 1H), 7.13 (app d, 2H), 7.35 (app d, 2H), 7.45 (br, 1H), 11.23 (br s, 1H).

Workup

  1. customThe reaction mixture was separated between with water (10 mL) and EtOAc (10 mL)
  2. extractionThe aqueous phase was back-extracted with EtOAc (3×10 mL)
  3. washthe combined organic phases were washed with a saturated NaCl solution (25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (SiO2; gradient from 20% EtOAc/80% pet. ether to 30% EtOAc/70% pet ether)

Sources & evidence

ORD record
ord-bb4714acbdb7431e91fab56c3e07b365
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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